Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) afforded the corresponding N1-2,6-disubstituted nucleosides (2a,b) without any trace of the N3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N1-6-methyluridine (4) and the corresponding N1-2-amino-6-methyl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown. © 2007 The Japan Institute of Heterocyclic Chemistry.
Stereoselective synthesis of N1-6-methyluridine and related 2-substituted analogues / Radi, Marco; Elena, Petricci; Federico, Corelli; Maurizio, Botta. - In: HETEROCYCLES. - ISSN 0385-5414. - 72:(2007), pp. 79-83.
Stereoselective synthesis of N1-6-methyluridine and related 2-substituted analogues
RADI, Marco;
2007-01-01
Abstract
Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) afforded the corresponding N1-2,6-disubstituted nucleosides (2a,b) without any trace of the N3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N1-6-methyluridine (4) and the corresponding N1-2-amino-6-methyl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown. © 2007 The Japan Institute of Heterocyclic Chemistry.| File | Dimensione | Formato | |
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